Boston reportedly offered Lester a four-year deal worth $70 million before the 2014 season, but the team ended up trading their homegrown left-hander to the Athletics at the '14 trade deadline. Lester signed a $155 million contract with the Cubs in free agency the ensuing offseason.

Henry once rationalized low-balling Lester by taking a stance against signing pitchers 30 and older. His point was moot once the team signed David Price to a seven-year contract in 2015.

"I think we blew the Jon Lester - we blew the signing in spring training," Henry said. "And for reasons that are pretty apparent now, which I won't go into, but they're apparent. But it wasn't… you can see what's gone on in free agency. The price of WAR has gone up radically that it's difficult, whether it's a pitcher or a position player, entering into a really long term contract with high dollars."

Henry was asked whether his "avoid signing pitchers age 30 and above" philosophy has evolved with both Price (33) and Sale (29) on the roster.

"I think Chris [Sale] falls out of the norm because he's just such a great - not just a great pitcher but a great part of the team as we saw in the World Series he had quite an impact just being on the bench during the World Series," Henry said.

"So he's a special player. We would love to be able to sign him. I think he would like to as well. But there are the realities of the marketplace in budgets and this is his opportunity to be a free agent, so, potentially … something could happen."

Although the Red Sox brass has indicated they likely won't be able to re-sign all of their players set to hit the market, their admittance of "blowing it" with Lester at least bodes well for the team's odds of getting it right with Sale.

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